Holiday rentals near Port of Leonardtown Winery
We found 353 holiday rentals — enter your dates for availability
If you are looking to stay near Port of Leonardtown Winery, take a look at holiday rentals to find the perfect home base for your trip. Whether you’re staying in a holiday home with your children or with friends, you'll find the amenities that you need and want, which might include parking and a washer and dryer. No matter what you're looking for, you're sure to find a property to rent that has what everyone needs, including a place that is accessible or non-smoking.
Holiday rentals with weekly discounts - Port of Leonardtown Winery
Showing deals for:10 Oct - 17 Oct
Image gallery for Secluded waterfront house to relax or enjoy water activities from private pier
9.8 out of 10 rating
Exceptional
(27 reviews)
Secluded waterfront house to relax or enjoy water activities from private pier
Cobb Island, MD
8% off
Price is AU$5,239
AU$748 per night
includes taxes & fees
Find spaces that suit your style
House
Condo/Apartment
Find the best place to stay - Port of Leonardtown Winery
Chesapeake Bay Waterfront View
Sleeps 7 · 3 bedrooms · 2+ bathrooms
9.8 out of 10
exceptional
Top rated rentals - Port of Leonardtown Winery
Fabulous serenity and comfort all in one.
10 out of 10
exceptional
(27 reviews)
We had a very comfortable and lovely stay at this extensive studio apartment. Lots of space, and all the necessary amenities to make it perfectly suitable for 2, 3, and maybe even up to 4 people if it’s family. Terrific!
Trina Y.
Stayed Oct 2024
Peace of mindOur Book with Confidence Guarantee gives you 24/7 support
More quality timeFrom booking to staying, the whole process is simple and enjoyable
All the privacy of homeEnjoy full kitchens, laundry, pools, gardens and more
More for lessMore space, more privacy, more amenities — more value